Sodium Thiosulfate → HCID 53236719, compound

HRID 1966686

Reaction equation

HRID 1966686 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([NH2:19])[C:11]([NH:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:12][CH:13]=2)=[CH:4][N:3]=1.[CH3:20][C:21]1[S:22][C:23]([C:27]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:28]=2[CH:29]=O)=[C:24]([CH3:26])[N:25]=1.OOS([O-])=O.[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C.O>[C:15]([N:14]1[C:11]2[CH:12]=[CH:13][C:8]([C:5]3[CH:4]=[N:3][C:2]([NH2:1])=[N:7][CH:6]=3)=[CH:9][C:10]=2[N:19]=[C:29]1[C:28]1[CH:31]=[C:32]([O:35][CH3:36])[CH:33]=[CH:34][C:27]=1[C:23]1[S:22][C:21]([CH3:20])=[N:25][C:24]=1[CH3:26])([CH3:16])([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 23707502Potassium hydroxy sulfiteHCID 585418994-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamineHCID 585420022-(2,4-Dimethyl-thiazol-5-yl)-5-methoxy-benzaldehyde

Product 1

HCID 53236719HCID 53236719, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine (100 mg, 0.39 mmol) in DMF (5 mL) is added 2-(2,4-dimethyl-thiazol-5-yl)-5-methoxy-benzaldehyde (144 mg, 0.58 mmol) at room temperature. Oxone (239 mg, 0.39 mmol) in H2O (1 mL) is added and the solution is stirred for 4 hours. Saturated sodium thiosulfate solution (5 mL) is added and the mixture is extracted with EtOAc (3×10 mL) and H2O (10 mL). The combined organic layer is dried with MgSO4 and is filtered. The filtrate is concentrated and the residue is purified by silica gel flash column chromatography eluting with 10% MeOH in CH2Cl2 to afford the title compound (81 mg, 43%) as a pale brown foam. LCMS (ESMS): m/z 485.72 (M++1)

Workup

  1. extractionthe mixture is extracted with EtOAc (3×10 mL) and H2O (10 mL)
  2. dry with materialThe combined organic layer is dried with MgSO4
  3. filtrationis filtered
  4. concentrationThe filtrate is concentrated
  5. customthe residue is purified by silica gel flash column chromatography
  6. washeluting with 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-cd15a7c7d9474ab8961fb4ebf8bd6bbd
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Linked notes

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